


Around and Around We Go

by enbyvalentine



Category: Supernatural
Genre: Action/Adventure, Angst and Hurt/Comfort, Blood and Gore, Christmas Fluff, Decapitation, Explicit Language, F/M, Gender Dysphoria, Gender or Sex Swap, Interlude, M/M, Original Character(s), Trans Male Character, butnotinakinkyway, deansaysf!ck, trans!Dean
Language: English
Status: In-Progress
Published: 2020-12-07
Updated: 2020-12-13
Packaged: 2021-03-09 21:08:08
Rating: Teen And Up Audiences
Warnings: Graphic Depictions Of Violence
Chapters: 2
Words: 3,873
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27853102
Author URL: https://archiveofourown.org/users/enbyvalentine/pseuds/enbyvalentine
Summary: A riddle obsessed monster hunts down innocent people, killing them for getting the riddle incorrect. Sam and Dean are busy hunting vampires, while Dean adjusts to his gender identity, learning to be comfortable with himself. Very angsty, bloody, and soft. This is my first fanfic, so I'm just figuring out the ropes. It's a fun practice run!
Relationships: Castiel/Dean Winchester
Comments: 2
Kudos: 4





	1. 1 - Autumn's End/Hunting Vampires

**Summary for the Chapter:**

> A riddle obsessed monster hunts down innocent people, killing them for getting the riddle incorrect. Sam and Dean are busy hunting vampires, while Dean adjusts to his gender identity, learning to be comfortable with himself. Very angsty, bloody, and soft. This is my first fanfic, so I'm just figuring out the ropes. It's a fun practice run!

# Around and Around We Go

### Chapter 1 - Autumn's End/Hunting Vampires

  
The whiskey burned in his stomach. He thought it was the whiskey, at least. His feet stumbled to the fridge, grabbing at the rusted handle. The grit from the ancient refrigerator snuck under his nails, giving texture the tips of his fingers.

He regretted the last three shots, the sleeping volcano of a cocktail brewing in his stomach. This isn't right, he thought. It wasn't supposed to feel like this. He'd had hundreds of hangovers in his life, even alcohol poisoning. Nothing had ever felt like this.

The sleeping volcano began to erupt. He didn't make it to the bathroom, vomiting all over the foyer instead. But it wasn't only the whiskey that came up. It was blood. And it kept coming.  
The wind rattled the windows, rain teasing the poorly insulated building.

He was going to die soaked, coughing up his own blood.

Stop being dramatic, he thought as he moved to the toilet basin.

The basin water didn't reflect him, however. A decomposed corpse stared back up at him. He would've screamed, but he was too busy coughing up his own blood.

**I can save you**. The voice rang like a gothic church bell in his head. **I can make it stop**.

"Please".

**First, you must answer a riddle.**

He figured there was no arguing. "Okay".

**What appears on many hands, and yet has holes in it?**

His brain computed for every possible answer. "What?"

**What follows you, but only moves in one direction?**

"I-I don't know."

A deep, satisfied growl, almost a purr. **You don't know?**

"I'm sorry- please-"

The decomposed face in the toilet began to fade away.

"Wait- no! What is it? Please! Make it stop!" 

The decomposed corpse gave a sadistic chuckle, proud of itself. 

"TELL ME WHAT IT IS. PLEASE. HELP ME!"

**The Moon**.

The man bowled over, unable to control his body. He convulsed on the bathroom floor, his brain a blown fuse.

A satisfied growl. The wind shoved open the bathroom window.

#### Somewhere In Washington.

They didn't hear it coming. The vampire pounced on them.

It leaped down from the trees. Sam's body hit the ground, tackled by the beast.

Dean raised his axe at it, pumping the axehead at the creature. The blade _wooshed_ over the vampire's head. It _spat _back.__

_____"_____ Come on, that's just gross," Dean said.

Sam raised a cross. The creature squirmed back. Dean was quick. He swung his axe, making contact with the base of the thing’s neck. A deadly hit. Or it should have been.

The creature’s head tiled askew, still connected by tendons and muscle. It kept on fighting, like some decapitated chicken.

Sam raised his shotgun. One shot was all it took. The creature’s head went flying - the body falling limp. Blood spurted in a lame imitation of a living thing.

Sam and Dean exchanged a look - both of them were in profound need of a nap.

####  ~~******* ~~

The boys opened the trunk of the impala, assessing their stock of weapons. "I hate fangs," Dean said, "Why do they have to hiss like that? It's not like they're fucking Nosferatu."  
  
"I just got this coat," Sam held up the remainders of his jacket, calcified by blood.  
  
Dean limped over the driver door, bruised and aching from the hunt. The front windshield of the Impala was caved in. The front seat was covered with dirt and glass.  
  
"Look at what they did to you," Dean cooed to the beaten car.  
  
Sam climbed in on the other side, having to climb through the window since the door was jammed shut, "You're going to have to take it in."  
  
"Nope. No way. I'm not letting some greasy stranger anywhere near my car. I just- I can't do that to her."  
  
Sam held back a laugh, knowing it would only anger Dean if he did, "you're emotional dependence on this car is a little weird, man."  
  
Yeah- well...," There wasn't a comeback. Dean started the car, the machine jittering at a concerning rate.

_Crash._ "Was that the hubcap?"

#### Three Months Earlier

Velvet. The smell of woodsmoke. Rain seeping in through the rafters. Leaves had blown in through the windows, pooling up together on the floor. Orange, maroon. A litany of colors.  
  
Cas snored, his head resting on Dean's chest. Dean gently ran fingers through his air. He felt light.  
  
A few hours later, the fire had burnt out and the room was frigid. Dean pulled Cas closer into him, not wanting to wake him and disrupt this gentle night.  
  
Was this real, or just another dream? Dean couldn't keep track anymore. Memory had muddied together every memory of Cas. It had been ages since he had seen him. _Since I've held him,_ the thought passed through Dean like a cold spot.

####  _Knock, Knock._

"Dean, you good?" Sam had become overprotective of Dean. It was sweet in a way, but overbearing. Sam was still adjusting, doing his best to make room for this new version of Dean. After Dean had come out, revealing himself to be man, Sam had done everything he could do to be accommodating. Sam never misidentified him. Never once suggested he perceived Dean to be anything other than himself.  
  
The initial conversation had been difficult. Telling Sam was more terrifying than the majority of monsters Dean had faced. It was the hypotheticals. The outcomes. The lack of certainty. The potential to lose Sam entirely, and be left with no-one and nothing in this life. But Dean had to do it. He had to be _Him._  
  
"I'm good, Sammy."  
  
"Hairy palms, Dean."  
  
Sam walked away, leaving Dean to his privacy.  
  
Dean unrolled the gauze that had serviced for flattening his chest. It had been torn to shreds. His chest was littered with cuts and minor open wounds. Trophies of the hunt. More additions to the constellation of scars covering his body.  
  
Soon enough, Dean had applied a new layer of gauze and several layers of baggy clothes.  
  
"I think I found something for us- it seems pretty interesting." Sam began, leaning into his computer.  
  
"What'd you find, Mr. Wizard Nerd?"  
  
Sam's nose wrinkled in disapproval, "bunch of teenagers got wasted, lost in the woods. Only a couple of them made it back. The others couldn't be found. The two survivors insisted they had been eaten."  
  
"Eaten?"  
  
Sam nodded sagely, "Eaten". He cleared his throat, "now here's the strange part. They couldn't say _what_ ate them, but they mentioned something about riddles."  
  
"Riddles?"  
  
"You ever hear of a sphinx?"  
  
"Yeah- crazy cat lion lady with wings and the sharp teeth? You're thinking one of those did this?"  
Sam nodded, despite the ludicrousness of his claim.  
  
"Well, I guess we'll have to go find out."


	2. Christmas Memories

**Summary for the Chapter:**

> Dean reminisces of past Christmas's while investigating a case. A college student survives a Sphinx attack, and is questioned by two different sets of FBI agents. We get some solid Destiel fluff, it is very angsty and soft.

#### A Long Time Ago

  
Sam and Dean were holed up with their father in a motel room for Christmas. It wasn't unusual for them to be stuck in cheap, sticky motel rooms. That was their life. Their home. It was, however, unusual for them to celebrate Christmas. Something had gotten into John that year, and he had decided he wanted to surprise the boys. He didn't tell either of the boys about it. It was one of the few times they had genuinely felt like a family.  
  
An old black and white movie played on the outdated tube TV. John was playing music on the radio, his favorite rock station. He slowly hummed along to it. Snow billowed outside. Sam was dead asleep. John had bought Sam his first few beers as part of his Christmas present. Sam had drank probably too much, and was now passed out after getting drunk for the first time. He had also gotten Sam a couple of books on creative writing, trying to support his son in something he had always been gifted in.  
  
Dean sat on the floor, covered in Christmas wrapping paper shreds. This was the last Christmas they would ever get to spend together, before Sam went off to college.  
  
He wiped away the fog from the window, trying to peer out. There was nothing. The snow hid everything. Only him, his dad, his brother, and the static from the tube TV.. Of course, Dean wasn't _Dean_ yet. Not officially, at least.  
  
This is the night I'm going to tell him, Dean thought. The sick realization weighed down his stomach. It was worse than the fear of any hunt or monster Dean had been up against, before or since.  
"What- got a problem with my music?" John had noticed Dean staring at him. Dean was always a dead giveaway.  
  
"No, there's just- there's something I need to tell you." John turned down the music - a respectful gesture.  
  
Dean looked over at the passed out Sam, who was dead asleep.  
  
John was getting curious, "Sam acting weird lately?"  
  
"No- it's not that."  
"What's up Deanne?"  
  
"Dean."  
  
John's voice took a stark seriousness, "What?"  
  
"My name is Dean. I'm a boy. My name is Dean Winchester."  
Dean stared at his hands, refusing to make eye contact with his father. He could feel John's eyes boring into him. "What?"  
"I-I'm a boy."  
John turned back to the road. Dean dared to sneak a glance at him. He had a confused expression, as if computing something. "Huh."  
_Huh?_ Dean had just confessed the scariest thing he could confess and his father responded with, _huh_?  
"Okay."  
"That's it?" Dean was almost disappointed by the anticlimax. Of all the scenarios he had played in his head, every single outcome he had predicted, this hadn't been one of them. He hadn't been expecting nonchalance.  
  
"What? Were you expecting something more Hallmark?"  
Dean shook his head, unsure how to respond.  
  
" _Dean..._ , I hunt monsters and ghosts for a living. You being a boy is definitely low on the list of weird shit I've dealt with. I mean, come on. You've always been my boy - I knew I never had a daughter."  
  
A wave of relief washed over him. He could feel his guard letting itself down.  
  
"Have you told Sammie?" His dad asked.  
"I mean- not yet. I was going to, but I also didn't want to freak him out."  
  
John nodded, and went back to the book of Mediterranean Mythologies he was reading.  
  
It was one of the best Christmas's Dean could remember, and the last one he had spent with his father and his brother there. Together.  


  


#### Republic, Washington.

####    


  
  
Dean drove through the heart of a tiny Washington town. It was surrounded on all sides by snowy forest, every business decked out in Christmas decorations.  
  
"God- I hate Christmas," Sam grimaced at the outdated town.  
  
"Are you kidding? Alcoholic eggnog, sexy Santa costumes. What's there not to love?"  
  
They pulled up to a cheap looking motel on the outskirts of town. "I don't know. I just hate Christmas music."  
  
"Ah- don't be a cynic Sammie."  
  
  
Dean gave the crime scene another once over, trying his best to appear as much of a detective as he could. The town Sheriff, Sheriff Trimbly, watched him anxiously. He wanted answers, and so did Dean.  
  
"No forced entry, that I can see," Dean mentioned to Sam. They were both amused by their Fed persona's. "Agent Perry, do you agree?"  
  
"Yes I do, Agent Robertson." They both wanted the Sheriff to leave so they could do the actual investigation. Take out the EMF's, scrub the house for any traces of sulfur.  
  
"Well, Trimbly, I'm not sure if we'll need your help anymore tonight. You can go home, it's been a late one."  
  
The Sheriff shook his head, respectfully declining. "No thanks- I don't like to leave agents alone at my crime scenes. It'd be disrespectful. If it's all the same to you."  
  
Dean and Sam exchanged a look. "I suppose that's just fine," Dean said.  
  
The dead body was half-submerged in the toilet. There was no signs of a physical altercation, no cuts or actual damage to the man's body. It was as if he had just drowned himself in the toilet.  
  
"And you didn't find anything- strange, or out of the ordinary?" Dean asked.  
  
"Well- nothing other than the unordinary amount of alcohol in the fridge. An elephant could drink itself to death with that much booze."  
  
Cops were difficult to deal with, not other than their stubbornness, but also because they didn't know what to look for. They were trained to only detect other humans, so picking evidence off of them was difficult, but not impossible.  
  
"Have been other deaths like this? Of the same kind."  
  
"Oh- uhm, there've been a couple, I suppose. Folks drowning themselves like this. You don't think it could be some sorta serial killer, do ya?"  
  
Dean shook his head. Sam gave him a subtle nod, both of them pleased to have found something useful out of this visit.  
  
Sam shook the sheriff's hand, and left the crime scene behind.  
  
They undid their ties, spiking the heater in the car. "So- no EMF signal, no sulfur. These people just drown themselves in their toilets? What kind of monster would do that?"  
  
"Well- at least there's a connection there."  
  
"Still think it's a sphinx?"  
  
Sam shrugged, "Could be anything. There's someone we need to go talk to, however."  
  
He passed Dean the folder, full of newspaper clippings and printed articles. The article Sam was presenting was about a college kid, Samantha Haddock, who'd been reportedly attacked by a perpetrator. "One who talks in riddles, I might add."  
  
"And she survived?"  
  
Sam nodded. Dean looked over it again, still not convinced. These were always his favorite ones, however. There was something challenging about a new creature. It made it feel fresh.  
  
Dean turned the key, the Impala's engine rumbling to life. The old car jumped forwards, moving as if it had just come off the line.  
  
Watching them drive away was a man wearing a long khaki overcoat, and a loose tie. A street light burst, and the angel was gone.  


  
  
The last time Dean had saw Cas was two years ago. On Christmas.  
  
It had been a difficult Winter. A job had gone wrong. Sam had been hurt. People had died. You couldn't save everyone all the time, and when you lost people the guilt was almost unbearable.  
  
Sam was in the hospital (Bobby's basement) and Dean had barely even left his side. Sam was in a coma, one that he'd been in for a while.  
  
"Cas, you know you can knock, right?" The angel had a disconcerting away of appearing unannounced.  
  
"I'm sorry, Dean."  
  
Dean looked over at him, begging for help. "Please- save him, wake him. Do something. Whip some angel dust out of your ass and save him."  
  
Cas looked remorseful. It always struck Dean by surprise whenever an expression broke across Cas's face. Cas moved forwards, and put his fingertips on Sam's forehead. Dean was always struck by the grace Cas moved with. His gentleness.  
  
"He is healing. He must rest. When he is ready, he'll wake."  
  
This was something. The best news Dean had heard in a while. "So he'll be okay?"  
  
Cas gave him a nod, and even followed it up with his attempt at a reassuring smile. It didn't work, but somehow that made it even more endearing to Dean.  
  
" _You_ need to rest, Dean."  
  
Dean turned back to Sam. He didn't want to leave his side. He wanted to be there when Sam woke up.  
  
"He'll be fine," Cas said, his hand resting on Dean's shoulder. Dean reached up and put his hand on Cas's. His hand was soft, and surprisingly small for Cas's height. Dean had always wondered how it would fit into his hand.  
  
"Come, go to bed." Cas led him up, practically carrying the beaten boy. Dean hadn't realized how deep in pain he was, every part of his body aching.  
  
They made it upstairs, to Bobby's bedroom. He'd surrendered his room to the boys, giving them a place to rest after they had practically collapsed on his doorstep. Bobby was snoring himself to death in the room next door.  
  
Cas gently helped Dean take off his jacket. He untied Dean's boots. He pulled back the covers as Dean crawled under them. Cas was the only person he would ever let care for him like this. Cas kneeled down, coming to his level.  
  
Dean shivered. Being this close to Cas made him feel home. A feeling he hadn't known for a long time.  
  
"You have such pretty eyes. A thing of beauty," Cas almost cooed.  
  
Dean didn't know what to say. He was always flustered when people complimented him. When Cas complimented him it was like trying to solve a wartime code. His brain couldn't process a reply.  
  
"I have to leave, Dean. For a while. You won't see me for a long time, under your measurements."  
  
"What does that mean, Cas?"  
  
Cas always looked like a painting when he was sad. "There is something following me. I don't want it catching onto to you. I've got to lose it, first."  
  
"Let us help you, Cas. We can handle them. Together"  
  
Cas gave him another one of those sad smiles that were worth a painting. "When you are both healed."  
Cas reached over, grabbing a glass of water from the nightstand. He offered it Dean, "You must be thirsty."  
  
Dean took the glass, downing the drink as fast as he could. He didn't realize how thirsty he was. Cas laughed, and put it the glass on the nightstand when it was empty.  
  
They looked at each other, both saying nothing. Dean felt so tired, and empty. All he wanted to do was fall asleep on Cas. Hold onto him.  
  
Cas leaned forward, kissing Dean's forehead. Dean wrapped his arms around Cas. "Can you please just stay tonight?"  
  
The angel smiled, "yes".  
  
Cas climbed under the covers, not discomforted by his layers of clothes.  
  
They held eachother for a while, glowing warm under the sheets. Dean felt exhaustion have it's way with him.  
  
Dean reached up, giving Cas one good kiss. Cas kissed him back, in a way that was sweet and giving.  
"How'd you learn to kiss like that," Dean asked.  
  
"I whipped out some of my angel dust, you would say." He said with a flirtatious self-flattery. Dean smiled, charmed by Cas's celestial awkwardness.  
  
Dean stole one more sleepy kiss. It was all he needed before passing out immediately. He didn't dream that night, or even stir at all.  
  
When he woke up that morning, Cas was gone, and Christmas was over.

  
Samantha Haddock was in her second year at the Spokane Community College in Republic. She had hated it there, but the living was cheap and it just so happened to be where life had landed her.  
Finals were done, the most bleak and relentless weak of the semester. Her brain felt stuffed with hieroglyphs, running test questions that had already been answered. When she had started hearing voices, she wasn't all that surprised. And once the surprise wore off, she wasn't impressed either."A riddle?" She asked the noncorporeal voice.  
"Yes," the voice answered, "Answer correctly and you live."  
This definitely had to be side effect of finals, she thought.  
"Then just do it- I've answered enough bullshit today."  
A splitting headache burst across her brain. A dark chuckle sounded from around her. Blood began gushing from her nose.  
  
This wasn't a hallucination, she thought. Or if it was, then it's pretty fucking convincing.  
  
"What's the riddle?" Sam begged, realizing she now had to answer for her life.  
  
"What has teeth, yet never bites?"  
Sam's brain rushed as much as it could, given the circumstances. "I don't know- more please?"  
  
"What roars, yet has no voice?"  
  
"I don't know- a fucking crowd?"  
  
The intangible thing chuckled, amused by her panic. "No."  
  
" _Then what is it?_ "  
Sam looked up, catching her reflection in a mirror. She screamed. Her face was rotting, the flesh hanging off. She reached up to feel her skin, but it felt normal.  
  
I'm having an absolute mental breakdown, she thought. She probably wouldn't even have minded going insane, it would have been much preferable to being killed by whatever this thing was.  
  
She could feel the intangible thing smiling, practically taunting her.  
  
"An jet engine." It said with dark glee. Her brain started to burn like one.  
  
"Wait- what? That- that doesn't make any sense- that's a trick question."  
  
The burning didn't quite stop, as much as it halted, waiting to be brought back for more.  
  
"What?"  
Sam lunged on the opening, "Jet engines don't have teeth- unless you're referring to their guns and their weapons, but that's in inaccurate comparison. You're just trying to throw me for a loop."  
The thing sighed, frustrated by this turn of events.  
  
"Maybe so." It said. The entire building shook. The sound of a distant, ancient bell rang, as the entity left her apartment.  
  
She ripped her baseball cap off, and ran to the bathroom. She opened the cupboard and reached for the baby aspirin.  
  
She poured them into her hand, downing a handful. Anything to stop the violent pain in her head.  
  
Sam recanted this story to the second pair of Federal Agents she had seen that day. She had long since stopped trying to convince authorities, not sparing any details in hope it would scare them off. Unfortunately, it didn't work on these two.

  
"And did you notice anything unusual earlier that night?" Dean asked.

Sam gave him an exasperated look. "What, other than the hallucinations and the fountain of blood gushing out my nose?"

"Well- we're talking about cold chills, or if you smelled sulfur, or something like that."

Sam looked between the two men. They both gave her serious looks. They had listened to her story, all of it, without questioning it. These men were different.

"No- I didn't. My brain was also fried from school, so I wasn't really paying attention to anything."  
There was a knock on the door.

"You expecting anybody?"

Sam shook her head.

The taller one (Agent Perry?) stood up and answered the door.

"Oh," an official woman's voice sounded, "I didn't know the Bureau had already assigned agents to this case."  
At the door was a short, red haired woman with a tall, floppy man. "Well, they did and they didn't. They just wanted us to be on sight to assist with anything you two might need." Agent Perry said to the woman.  
The woman turned the man, muttering something to him. "Scully- at least they're letting us follow through with the investigation," the man said.

Scully (Sam had assumed that was the woman's name) turned back to Agent Perry. She entered, stepping around him into the space. "Thank you for the help, gentlemen. We'll let you know if we need anything else."

Agent Perry and Agent Robertson both seem flustered at being discarded so quickly, but made their way out without protest.

"Samantha Haddock, is it?" The man asked in an informal tone.

Sam nodded.

The two new agents flashed their badges. "I'm Agent Mulder, this is Agent Scully. We'd like to ask you a couple questions about what happened to you a few days ago."  



End file.
